Arylsulonamidopyrazole and imidazole intumescent coated articles

ABSTRACT

Intumescent compositions of the invention comprise certain arylsulfonamidopyrazoles and imidazoles, such as 3sulfanilamidopyrazole, 2-sulfanilamidoimidazole, and derivatives thereof. The intumescent agents may be employed in conjunction with additives conventionally used in intumescent compositions. Articles coated with these intumescent compositions are also described.

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x12 sumqmm nited Stat Roth QYL/SEARCH. ROOM nu 3,769,076 [451' Oct. 30, 1973 sussmu IMIDAZOLE INTUMESCENT COATED ARTICLES i inventor: Shirley ll. Roth, Highland Park, NJ.

Assignee:

N.Y. I

Filed: Feb. 22, 1972 Appl. No.: 228,384

US. Cl. 117/136, 106/15 FP Int. Cl. C09d 5/18, C091: 3128 Field of Search 117/136; 106/15 FP;

I References Cited UNITED STATES PATENTS 3,535,130 10/1970 Webb 117/136 X Cities Service Company, New York,

v I OTHER PUBLICATIONS Northey, Sulfonamides, p. 30 and Table 27.( 1948).

- Primaryfxaminer-William-D. Martin Assistant Examiner-Harry T. Gw'innell Attorneylatricia J. Hogan et a1.

' ABSTRACT: I

luminescent compositions of the invention comprise certain arylsulfonamidopyrazoles and imidazoles, such as 3-sulfanilamidopyrazole, Z-su'lfa'niiamidoimidazole, and derivatives thereof. The intumescent agents may be employed in conjunction with additives convenv tionaliy used in intumescent compositions. Articles coated with these intumescent compositions are also described.

7 Claims, No Drawings ARYLSULONAMIDOPYRAZOLE AND IMIDAZOLE INTUMESCENT COATED ARTICLES BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to intumescentcompositions and more particularly relates to such compositions containing a one-component intumescent agent.

2. Description of the Prior Art g It is known that a substrate may be protectedfrom heat and fire by the application of an intumescent com:

position. intumescent compositions of the prior art usually contain an intumescent agent having at least three components; i.e., a carbonific, a spumific, and a catalyst; and they are typically characterized by the disadvantages of high cost, low spreading rate, relatively poor efficiency, poor water resistance, and poor weather-ability.

As disclosed in U. S. Pat. No. 3,535,130, it has already been discovered that a one-component intumescent agent has advantages over multicomponent intumescent agents. However, the intumescent agents of the patent have poor adherence to substrates and have an undesirable degree of moisture sensitivity.

[SUMMARY OF THE INVENTION An object of this invention is to'provide a novel class of one-component intumescent agents.

Another object is to provide such intumescent agents a low level of moisture sen; I

having good efficiency and sitivity.

These and other objects are attained by using as intu mescent agents compounds corresponding to the formula:

wherein Ar is a divalent aromatic residue, R is hydrogen, hydrocarbon, halohydrocarbon, or acyl, and R" is a pyrazolyl, substituted pyrazolyl, imidazolyl, or substituted imidazolyl radical.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The intumescent agents of the-invention may be any compounds corresponding to the above formula. How-' ever, they are preferably compounds whereinfArisla substituted pyrazolyl and imidazolyl radicals most commonly found in these compounds are the chloro, bromo, carboxy, hydroxy, amino, thio, sulfonamido,

C --C; alkyl, C -C alkoxy, phenyl, and'benzo deriva- I I tives,but compounds containing other substituted py-' razolyl or-imidazolylradicals are also utilizable. When A R" is a substituted pyrazolyl or imidazolyl radical, the

nitrogenof the sulfonamide group may be attached directly'to the' pyrazole or imidazole ring, or it may beat-.5 tached toythering through the substituent. Exemplary of the intumescent agents of the invention are 3-sulfanilamidopyraz'ole', 2-sulfanilamidoimidazole, 3-(4-amino-3-chlorobenzenesulfonamido)pyrazole, 3-

. (2-amino-4-bromobenzenesulfonamido )pyrazole, .3-

(4 amino-2-ethylbenzenesulfonamido)pyrazole, 3-( 3- amino-4-chloromethylbenzenesulfonamido)pyrazole,

' '(4-phenylaminobenzenesulfonamido)pyrazoie,

- sulfanilamidopyrazole, 3-sulfanilamidoaminopyrazole, 5-diethylamino-3- ic'nown techniques. For use in protectinga substrate from heat and fire,

divalent aromatic residue derived from benzene or naphthalene or an alkyl, haloal kyl, alkoxy, haloalkoxy, if halo, hydroxy, carboxy, amino, amido, or nitro deriva- 3-(4-amino-2-butoxybenzenesulfonamido)pyrazole, 3-(4-amino-3-chloromethoxybenzenesulfonamido pyrazole, 3-( 4-amino-3-hydroxybenzenesulfonamido)- pyrazole, 3-(4-amino 3-carb0xybenzenesulfonamido)- pyrazole, v3-(3,4-diaminobenzenesulfonamido)- pyrazole, 3-(4-amino-2- acetamidobenzenesulfonamido)-pyrazole, 3-(2-amin0- 4-nitrobenzenesulfonamido)pyrazole, v 3-(4- methylaminobenzenesulfonamido )pyrazole, 3-( 4- chloroethylaminobenzenesulfonamido)pyrazole, 3-(4 bromomethylaminobenzenesulfonamido)pyrazole, 3- 3-[4- (p-chiorophenylamino)benzenesulfonamido ]pyrazole,

3l4-(p-bromophenylamino)- b enzenesulfonamidolpyrazole, 3-( pacetamidobenzenesulfonamido)pyrazole, 3-(p-benzamidobenzenesulfonamido)-pyrazole, 5-chloro-3- sulfanilamidopyrazole, 5-bromo-3- 4-ethylcarboxy-3- 5-hydroxy-3- sulfanilamidopyrazole, sulfanilamidopyrazole,

5-amino-3-sulfanilamidopyrazole, sulfanilamidopyrazole, sulfanilamidopyrazole,

5-ethylthio-3- 5-(4-aminophenylsulfonamido)-3-sulfanilamidopyrazole, 5-methyl-3- sulfanilamidopyrazole, I 1 5-ethoxy-3- sulfanilamidopyrazole, 5-phenyl-3- sulfanilamidopyrazole, 3-methyll-phenyl-S- sulfanilamidopyrazole; 2-phenyl-3- sulfanilamidopyrazole," 3ssulfanilamidobenzopyrazole, the corresponding naphthalene compounds, the corresponding derivatives of imidazole, etc. When not readily available, these compounds may be prepared by the intumescent agents of the invention maybe applied in any suitable manner,-e.g.', electrodeposition, spraying of powdered intumescent agent onto an adhesive substrate, etc. However, it is usually preferred to compound the intumescent agent witha binder, e.g., nitrocellulose, and optionally also with one or more of the other ingredients conventionally used in intumescent compositions, e.g.,- stabilizers, dispersing agents, pigmerits, 'driers, biocides, anti-foamers, thickeners, protective colloids, fillers, blowing agents, etc.; disperse the composition in a suitable liquid medium, e.g., water 1 or a solvent or solvent mixture; and apply the coating te'cted. As is the case with conventional intumescent coatin'g.compositions, it is frequently convenient to R" is preferably a pyrazolyl or imidazolyl radical, but

it may bear one or more substituents if desired. Thecompositionthus formed to the substrate to be proapply these coating compositions in the form of a paint having a solids content of about -70 percent by weight and an intumescent agent/binder weight ratio of about 0.075-14/1 to deposit a coating having a dry thickness of about 0.00l-0.75 inch. I

The intumescent agents of the invention are efficient,

have low moisture sensitivity, and intumesce to form v foams having good volume, cell structure, and adher-' ence to substrates, such as wood, metal, and plastics." j-j They are also useful as flame retardants flammable compositions.

The following example is given to illustrate the invention and is not intended as a limitation thereof.

in normally EXAMPLE I 7 Place one gram of 3-sulfanilamidopyrazole in an aluminum pan and flame it with a propane torch. The

compound intumesces to form an excellent volume of foam having a good cell structure.

Similar results 7 are also observed when 2- sulfanilamidoimidazolc, sulfanilamidopyrazole, 2-phenyl-3- sulfanilamidopyra zole, and the other intumescent 3-methyll -phenyl-5- agents mentioned in the specification are substituted for-the intumescent agents of the Example.

It is obvious that many variations may be made in the products and processes set forth above without depart-' ing from the spirit and scope of this invention. i claim:

1. An article comprising a substrate coated with an intumescent agent corresponding to the formula:

wherein Ar is a divalent aromatic residue, R is hydrogen, hydrocarbon, halohydrocarbon, or acyl, and R" is a pyrazolyl, substituted pyrazolyl, imidazolyl, or substituted imidazolyl radical.

2. The article of claim 1 wherein Ar is a divalent aro- I matic residue derived from benzene or naphthalene or an alkyl, haloalkyl, alkoxy, haloalkoxy, halo, hydroxy, carboxy, amino, amido, or nitro derivative thereof. I

3. The article of claiml wherein R" is a pyrazolyl or l 1 imidazolyl radical or an alkyl, phenyl, or. benzoderiva tive thereof; 7 4. The article of claim 1 wherein the intumescent agent is 3-sulfanilamidopyrazole.

5. The article of claim 1 wherein the intumescent agent is Z-suIfanilamidoirnidazole.

6. The article of claim 1 wherein the intumescent agent is 3-methyll -phenyl-5-sulfanilamidopyrazole.

7. The article of claim 1 wherein the intumescent agent isZ-phenyl-3'sulfanilamidopyrazole. 

2. The article of claim 1 wherein Ar is a divalent aromatic residue derived from benzene or naphthalene or an alkyl, haloalkyl, alkoxy, haloalkoxy, halo, hydroxy, carboxy, amino, amido, or nitro derivative thereof.
 3. The article of claim 1 wherein R'''' is a pyrazolyl or imidazolyl radical or an alkyl, phenyl, or benzo derivative thereof.
 4. The article of claim 1 wherein the intumescent agent is 3-sulfanilamidopyrazole.
 5. The article of claim 1 wherein the intumescent agent is 2-sulfanilamidoimidazole.
 6. The article of claim 1 wherein the intumescent agent is 3-methyl-1-phenyl-5-sulfanilamidopyrazole.
 7. The article of claim 1 wherein the intumescent agent is 2-phenyl-3-sulfanilamidopyrazole. 